ES2592273T3 - Dihidropiridopirimidinas y dihidropiridazinas sustituidas con 5-arilo y su uso como antagonistas mineralocorticoides - Google Patents
Dihidropiridopirimidinas y dihidropiridazinas sustituidas con 5-arilo y su uso como antagonistas mineralocorticoides Download PDFInfo
- Publication number
- ES2592273T3 ES2592273T3 ES07725586.7T ES07725586T ES2592273T3 ES 2592273 T3 ES2592273 T3 ES 2592273T3 ES 07725586 T ES07725586 T ES 07725586T ES 2592273 T3 ES2592273 T3 ES 2592273T3
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- mmol
- methyl
- formula
- dmso
- nmr
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- 239000002394 mineralocorticoid antagonist Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 abstract description 63
- -1 amino, methoxy Chemical group 0.000 abstract description 13
- 229910052786 argon Inorganic materials 0.000 abstract description 10
- 150000003839 salts Chemical class 0.000 abstract description 4
- 239000012453 solvate Substances 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000000034 method Methods 0.000 description 41
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 38
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 14
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- 238000010992 reflux Methods 0.000 description 13
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
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- 238000011282 treatment Methods 0.000 description 7
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
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- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000002953 preparative HPLC Methods 0.000 description 5
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 5
- 238000011321 prophylaxis Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- LZEQPLQXONZZJQ-UHFFFAOYSA-N 3-[(2-methyl-4-oxochromen-8-yl)methylidene]pentane-2,4-dione Chemical compound O1C(C)=CC(=O)C2=C1C(C=C(C(=O)C)C(C)=O)=CC=C2 LZEQPLQXONZZJQ-UHFFFAOYSA-N 0.000 description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 206010020571 Hyperaldosteronism Diseases 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
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Classifications
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/42—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of mineralocorticosteroids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006026583 | 2006-06-07 | ||
| DE102006026583A DE102006026583A1 (de) | 2006-06-07 | 2006-06-07 | Aryl-substituierte hetero-bicyclische Verbindungen und ihre Verwendung |
| PCT/EP2007/004690 WO2007140894A1 (de) | 2006-06-07 | 2007-05-25 | 5-aryl-substituierte dihydropyridopyrimidine und dihydropyridazine und ihre verwendung als mineralkorticoidanatgonisten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2592273T3 true ES2592273T3 (es) | 2016-11-29 |
Family
ID=38462534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07725586.7T Active ES2592273T3 (es) | 2006-06-07 | 2007-05-25 | Dihidropiridopirimidinas y dihidropiridazinas sustituidas con 5-arilo y su uso como antagonistas mineralocorticoides |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8399471B2 (de) |
| EP (1) | EP2035419B1 (de) |
| JP (1) | JP5306999B2 (de) |
| CA (1) | CA2654313C (de) |
| DE (1) | DE102006026583A1 (de) |
| ES (1) | ES2592273T3 (de) |
| WO (1) | WO2007140894A1 (de) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006026585A1 (de) * | 2006-06-07 | 2007-12-13 | Bayer Healthcare Aktiengesellschaft | Substituierte 4-Aryl-1,4-dihydro-1,6-naphthyridine und ihre Verwendung |
| DE102007009494A1 (de) * | 2007-02-27 | 2008-08-28 | Bayer Healthcare Ag | Substituierte 4-Aryl-1, 4-dihydro-1,6-naphthyridinamide und ihre Verwendung |
| EP3593802A3 (de) | 2010-05-26 | 2020-03-25 | Satiogen Pharmaceuticals, Inc. | Gallensäurerückflusshemmer zur behandlung von diabetes, adipositas und entzündlichen magen-darm-erkrankungen |
| SG10201903512SA (en) | 2011-10-28 | 2019-05-30 | Lumena Pharmaceuticals Inc | Bile Acid Recycling Inhibitors For Treatment Of Pediatric Cholestatic Liver Diseases |
| US20130109671A1 (en) | 2011-10-28 | 2013-05-02 | Lumena Pharmaceuticals, Inc. | Bile Acid Recycling Inhibitors for Treatment of Pediatric Cholestatic Liver Diseases |
| CA2875986C (en) | 2012-06-04 | 2020-06-09 | Pharmacyclics, Inc. | Crystalline forms of a bruton's tyrosine kinase inhibitor |
| CA2907214A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of barrett's esophagus and gastroesophageal reflux disease |
| CA2907230A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of primary sclerosing cholangitis and inflammatory bowel disease |
| CA2956529A1 (en) | 2014-08-01 | 2016-02-04 | Bayer Pharma Aktiengesellschaft | Method for the preparation of (4s)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1-6-naphthyridine-3-carbox-amide and the purification thereof for use as an active pharmaceutical ingredient |
| CN106573002A (zh) | 2014-08-07 | 2017-04-19 | 药品循环有限责任公司 | 布鲁顿氏酪氨酸激酶抑制剂的新型制剂 |
| IL315294A (en) | 2015-03-03 | 2024-10-01 | Pharmacyclics Llc | Pharmaceutical formulations of bruton's tyrosine kinase inhibitor |
| CA2995949A1 (en) * | 2015-08-21 | 2017-03-02 | Bayer Pharma Aktiengesellschaft | Method for the preparation of (4s)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1-6-naphthyridine-3-carboxamide and recovery of (4s)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1-6-naphthyridine-3-carboxamide by electrochemical methods |
| PT3337800T (pt) * | 2015-08-21 | 2019-08-05 | Bayer Pharma AG | Método para a preparação de (4s)-4-(4-ciano-2-metoxi fenil)-5-etoxi-2,8-dimetil-1,4-di-hidro-1-6-naftiridina-3- carboxamida e purificação do mesmo para a utilização como ingrediente farmacêutico ativo |
| EP3798219A4 (de) * | 2018-05-22 | 2022-02-09 | Sunshine Lake Pharma Co., Ltd. | Phenylsubstituierte dihydronaphthyridinverbindung und verwendung davon |
| BR112021015815A2 (pt) | 2019-02-12 | 2022-01-18 | Mirum Pharmaceuticals Inc | Métodos para tratar colestase |
| CN113549066B (zh) * | 2020-04-24 | 2023-07-21 | 年衍药业(珠海)有限公司 | 二氢萘啶类化合物的晶型及其用途 |
| CN113549067B (zh) * | 2020-04-24 | 2023-10-03 | 年衍药业(珠海)有限公司 | 二氢萘啶类化合物的晶型及其用途 |
| CN117836295A (zh) * | 2021-09-18 | 2024-04-05 | 上海拓界生物医药科技有限公司 | 取代的1,4-二氢-1,6-萘啶酰胺及其用途 |
| EP4286368A1 (de) | 2022-05-31 | 2023-12-06 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 4-formyl-3-methoxybenzonitril |
| WO2024022481A1 (zh) * | 2022-07-29 | 2024-02-01 | 苏中药业集团股份有限公司 | 苯基取代的二氢萘啶类化合物及其制备与用途 |
| CN119684288A (zh) * | 2024-12-18 | 2025-03-25 | 安徽先和医药研究有限公司 | 非奈利酮的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4698341A (en) | 1983-07-30 | 1987-10-06 | Godecke Aktiengesellschaft | Use of 1,6-naphthyridinone derivatives in treating pulmonary thrombosis |
| DE3502831A1 (de) | 1985-01-29 | 1986-07-31 | Gödecke AG, 1000 Berlin | 1,6-naphthyridinon-derivate, verfahren zu deren herstellung und deren verwendung |
| DE3327650A1 (de) | 1983-07-30 | 1985-02-14 | Gödecke AG, 1000 Berlin | 1,6-naphthyridinon-derivate, verfahren zu deren herstellung und deren verwendung bei der bekaempfung von gefaesserkrankungen |
| US4760081A (en) | 1984-08-25 | 1988-07-26 | Goedecke Aktiengesellschaft | 1,6-naphthyridine derivatives useful for treating diseases of the blood vessels |
| DE3431303A1 (de) | 1984-08-25 | 1986-02-27 | Goedecke Ag | 1,6-naphthyridin-derivate, verfahren zu deren herstellung und deren verwendung |
| IL75987A (en) | 1984-08-25 | 1991-07-18 | Goedecke Ag | Tri-and tetrasubstituted-1,4-dihydro-1,6-naphthyridine-3-carboxylic acid derivatives,their preparation and pharmaceutical compositions containing them |
| DE3438351A1 (de) | 1984-10-19 | 1986-04-24 | Gödecke AG, 1000 Berlin | 4-alkoxy-pyrido(2,3-d)pyrimidin-derivate, verfahren zu deren herstellung und deren verwendung |
| DE3501696A1 (de) * | 1985-01-19 | 1986-07-24 | Bayer Ag, 5090 Leverkusen | Pyridopyrimidine, mehrere verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| IT1229118B (it) * | 1988-07-29 | 1991-07-22 | Simes | Composti attivi sul sistema cardiovascolare che presentano sia la struttura dei beta-bloccanti sia una porzione calcio-antagonista |
| WO2002010164A2 (en) | 2000-08-02 | 2002-02-07 | Abbott Laboratories | Dihydronaphthyridine- and dihydropyrrolopyridine-derivated compounds as potassium channel openers |
| DE102004012365A1 (de) * | 2004-03-13 | 2005-09-29 | Bayer Healthcare Ag | Substituierte Dihydropyridine |
| JP2007230869A (ja) | 2004-04-05 | 2007-09-13 | Takeda Chem Ind Ltd | アルドステロン受容体拮抗剤 |
| AU2005316511B2 (en) | 2004-12-13 | 2009-12-03 | Irm Llc | Compounds and compositions as modulators of steroidal receptors and calcium channel activities |
| DE102005034264A1 (de) | 2005-07-22 | 2007-02-01 | Bayer Healthcare Ag | 4-Chromenonyl-1,4-dihydropyridincarbonitrile und ihre Verwendung |
| DE102006026585A1 (de) | 2006-06-07 | 2007-12-13 | Bayer Healthcare Aktiengesellschaft | Substituierte 4-Aryl-1,4-dihydro-1,6-naphthyridine und ihre Verwendung |
| WO2010075068A1 (en) * | 2008-12-16 | 2010-07-01 | Schering Corporation | Pyridopyrimidine derivatives and methods of use thereof |
-
2006
- 2006-06-07 DE DE102006026583A patent/DE102006026583A1/de not_active Withdrawn
-
2007
- 2007-05-25 ES ES07725586.7T patent/ES2592273T3/es active Active
- 2007-05-25 US US12/303,369 patent/US8399471B2/en not_active Expired - Fee Related
- 2007-05-25 CA CA2654313A patent/CA2654313C/en not_active Expired - Fee Related
- 2007-05-25 EP EP07725586.7A patent/EP2035419B1/de not_active Not-in-force
- 2007-05-25 JP JP2009513573A patent/JP5306999B2/ja not_active Expired - Fee Related
- 2007-05-25 WO PCT/EP2007/004690 patent/WO2007140894A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP5306999B2 (ja) | 2013-10-02 |
| JP2009539784A (ja) | 2009-11-19 |
| US8399471B2 (en) | 2013-03-19 |
| EP2035419A1 (de) | 2009-03-18 |
| US20100035902A1 (en) | 2010-02-11 |
| EP2035419B1 (de) | 2016-06-22 |
| CA2654313C (en) | 2015-03-31 |
| DE102006026583A1 (de) | 2007-12-13 |
| CA2654313A1 (en) | 2007-12-13 |
| WO2007140894A1 (de) | 2007-12-13 |
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